反応 #3098

ord-9216403abe2a471cb8b491c2ec69c28c

反応方程式

C=[N+]=[N-]
diazomethane
Cl
Hydrogen chloride
C1COCCO1
dioxane
O=C(Cl)C(=O)Cl
oxalyl chloride
CCCC(CCC)C(=O)O
2-propylpentanoic acid
CCCC(CCC)C(=O)CCl
1-Chloro-3-propyl-2-hexanone

反応条件

温度
0°CELSIUS
詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    温度while warming to ambient temperature
  2. 2
    温度The mixture was cooled to 0° C.
  3. 3
    workup.STIRRINGThe reaction mixture was stirred 18 hours
  4. 4
    温度while warming to ambient temperature
  5. 5
    洗浄The reaction mixture was washed with 1M aqueous sodium carbonate solution (30 mL)
  6. 6
    乾燥dried over anhydrous sodium sulfate
  7. 7
    ろ過filtered
  8. 8
    濃縮concentrated under reduced pressure
  9. 9
    workup.DISSOLUTIONThe residue was dissolved in ether (2mL)
  10. 10
    温度cooled to 0° C. under a nitrogen atmosphere
  11. 11
    workup.STIRRINGThe reaction was stirred 18 hours
  12. 12
    温度while warming to ambient temperature
  13. 13
    濃縮The reaction mixture was concentrated under reduced pressure
  14. 14
    その他the residual oil was used in the next step without further purification

実験手順

To 2-propylpentanoic acid (156.6 μl, 1.00 mmol) dissolved in anhydrous dichloromethane (2 mL) was added DMF (3 μL, 4 mole %), and the solution was cooled to 0° C. under a nitrogen atmosphere. To the solution was added oxalyl chloride (94.3 μL, 1.08 mmol) dropwise over a few minutes. The reaction was stirred 18 hours while warming to ambient temperature. The mixture was cooled to 0° C. and excess ~0.3M ethereal diazomethane solution was added. The reaction mixture was stirred 18 hours while warming to ambient temperature. The reaction mixture was washed with 1M aqueous sodium carbonate solution (30 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was dissolved in ether (2mL) and cooled to 0° C. under a nitrogen atmosphere. Hydrogen chloride as a 4N solution in dioxane (275 μL, 1.10 mmol) was added dropwise over a few minutes. The reaction was stirred 18 hours while warming to ambient temperature. The reaction mixture was concentrated under reduced pressure and the residual oil was used in the next step without further purification.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US05731434uspto-grants-1998_03